The Hubris Hall of Fame

Billionaire investor Steve Cohen (the subject of a sweeping article in Vanity Fair’s June issue) received some more unneeded attention this March. Grappling with the implications of the government’s seven-year investigation into insider trading, Cohen no sooner had offered the Securities and Exchange Commission $616 million (a record in the securities industry) to settle only two charges before news broke that he had paid $155 million (a record for a U.S. collector) for a Picasso. This type of foot-in-mouth spending, however, is not unique to Cohen; when it comes to buyer’s remorse, few know it better than the rich and feckless. Herewith, a history of unwise purchases made by the desperately rich.

Lou Pearlman

The plan: Lou “Big Poppa” Pearlman was a con man long before he began assembling and swindling the boy bands of the early aughts; his $317 million Ponzi scheme started to unravel when his clients realized just how little they were being paid (and, perhaps, when they grew tired of his lecherous advances). The Backstreet Boys sued for income withheld in 1998, and ‘N Sync followed their lead in 1999.

The purchase: He bought a 12,000-square-foot lakeside mansion in a suburb outside Orlando (boy band Xanadu), two condominiums in Orlando proper and another nearby in Clearwater, two Vegas penthouses, a home in Hollywood, and an apartment in Manhattan.

The price: Pearlman fled the country in January 2007, only to be caught at Bali’s Westin Nusa Dua resort, registered under the name A. Incognito Johnson. He was sentenced to 25 years in prison, roughly one month for every million dollars he stole.